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I. Kinetic and mechanistic study of the (4+4) dimerization of 2,3-dimethylene-2,3-dihydrofuran. II. Preparation of 2,3-dimethylene-2,3-dihydrogenzo(b)furan by the flash vacuum pyrolysis of 2-methyl-3-benzo(b)furylmethyl benzoate. III. Reaction of 2,3-dimethylene-2,3-dihydrofuran with triplet oxygen

Technical Report ·
OSTI ID:5949736
A kinetic and mechanistic study of the (4+4) dimerization of 2,3-dimethylene-2,3-dihydrofuran (A) has been carried out based on the secondary deuterium kinetic isotope effects (2/sup 0/ D KIE), substituent effects and solvent effects. The 2/sup 0/ D KIE was studied by measuring the rate constants, k/sub 1/, k/sub 2/, k/sub 3/ and k/sub 4/, respectively, for the (4+4) dimerization of A, 2-methylene-3-dideuteriomethylene-2,3-dihydrofuran (B), 2-dideuteriomethylene-3-methylene-2,3-dihydrofuran (C) and 2,3-bis-(dideuteriomethylene)-2,3-dihydrofuran (D). 2-3-Dimethylene-2,3-dihydrobenzo(b)furan (E) was synthesized by the flash vacuum pyrolysis of 2-methyl-3-benzo(b)furylmethyl benzoate. The chemical reactions of E, which were investigated in this study, include thermal dimerization reactions and Diels-Alder reactions. The dimerization reaction of E gave both (4+2) and (4+4) dimers. The formation of cyclic peroxides from the reactions of A and its 5-methyl and 5-tert-butyl derivatives with triplet oxygen was investigated. Thermolysis of a cyclic peroxide gave dialdehyde, hydroxy aldehyde and diol as the products. 150 references, 28 figures, 70 tables.
Research Organization:
Ames Lab., IA (USA)
DOE Contract Number:
W-7405-ENG-82
OSTI ID:
5949736
Report Number(s):
IS-T-1186; ON: DE85009234
Country of Publication:
United States
Language:
English

Similar Records

I. Kinetic and mechanistic study of the (4+4) dimerization of 2,3-dimethylene-2,3-dihydrofuran. II. Preparation of 2,3-dimethylene-2,3-dihydrobenzo(B)furan by the flash vacuum pyrolysis of 2-methyl-3-benzo(B)furylmethyl benzoate. III. Reaction of 2,3-dimethylene-2,3-dihydrofuran with triplet oxygen
Thesis/Dissertation · Mon Dec 31 23:00:00 EST 1984 · OSTI ID:6036372
Preparation of 2,3-dimethylene-2,3-dihydrofurans by the flash vacuum pyrolysis of substituted furylmethyl esters
Journal Article · Tue Nov 03 23:00:00 EST 1981 · J. Am. Chem. Soc.; (United States) · OSTI ID:5637975
(4 + 4) dimerization of 2,3-dimethylene-2,3-dihydrofuran: secondary deuterium kinetic isotope effect evidence of a two-step mechanism
Journal Article · Wed Jul 09 00:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States) · OSTI ID:5585181

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
ALDEHYDES
ALKANES
ALKENES
AROMATICS
BENZENE
BENZOFURANS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CYCLOALKENES
DATA
DECOMPOSITION
DEUTERIUM
DIELS-ALDER REACTION
DIMERIZATION
ESTERS
EXPERIMENTAL DATA
FURANS
GEL PERMEATION CHROMATOGRAPHY
GLYCOLS
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HIGH VACUUM
HYDROCARBONS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INFORMATION
INFRARED SPECTRA
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
KINETICS
LIGHT NUCLEI
MAGNETIC RESONANCE
METHANE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
PEROXIDES
POLYMERIZATION
PYROLYSIS
PYROLYSIS PRODUCTS
REACTION KINETICS
RESONANCE
SEPARATION PROCESSES
SPECTRA
STABLE ISOTOPES
SYNTHESIS
THEORETICAL DATA
THERMOCHEMICAL PROCESSES